Diisopropylethylamine → N6-(2-{[7-(2,4-Dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}propyl)-3-nitropyridine-2,6-diamine

HRID 2171565Notes

Reaction equation

HRID 2171565 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:21]=[C:20]([NH:22][CH:23]([CH3:26])[CH2:24][NH2:25])[N:19]2[CH:27]=[CH:28][N:29]=[C:18]2[CH:17]=1.[NH2:30][C:31]1[C:36]([N+:37]([O-:39])=[O:38])=[CH:35][CH:34]=[C:33](Cl)[N:32]=1.C(N(CC)C(C)C)(C)C>>[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16]1[N:21]=[C:20]([NH:22][CH:23]([CH3:26])[CH2:24][NH:25][C:33]2[N:32]=[C:31]([NH2:30])[C:36]([N+:37]([O-:39])=[O:38])=[CH:35][CH:34]=2)[N:19]2[CH:27]=[CH:28][N:29]=[C:18]2[CH:17]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 131729958N2-[7-(2,4-Dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]propane-1,2-diamine trifluoracetate

Product 1

HCID 59312931N6-(2-{[7-(2,4-Dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}propyl)-3-nitropyridine-2,6-diamine

Procedure

N6-(2-{[7-(2,4-Dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}propyl)-3-nitropyridine-2,6-diamine (Example 83) is prepared in analogy to Example 82 from Example 37A (300 mg, 0.47 mmol), 2-amino-6-chloro-3-nitropyridine (161 mg, 0.93 mmol) and N,N-diisopropylethylamine (600 mg, 4.6 mmol). The crude product is reprecipitated from N,N-dimethylformamide and acetonitrile. The product is filtered off and washed with acetonitrile and dried. 99 mg (45% of theory) of the product are obtained as a solid.

Workup

  1. customThe crude product is reprecipitated from N,N-dimethylformamide and acetonitrile
  2. filtrationThe product is filtered off
  3. washwashed with acetonitrile
  4. customdried
  5. custom99 mg (45% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-7706035c652a46ad9b5aaf3f8250ce67
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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